Abstract
The structures of mono, di, and tri-O-methyl derivatives of 2,4,6-trinitrophloroglucinol were determined by single crystal X-ray diffraction. As the number of methoxy groups increased from one to three the unit cell volume increased at a rate greater than the formula weight of the asymmetric unit such that crystal density decreased from 1.823 to 1.619 Mg/m3. The structural data reveal that the decreased density is related to increased angles between the plane of the phenyl ring and the planes defined by the nitro and methoxy groups, as well as fewer inter molecular interactions.
Graphical Abstract
The structures of mono, di, and tri-O-methyl derivatives of 2,4,6-trinitrophloroglucinol were determined by single crystal X-ray diffraction. As the number of methoxy groups increased from one to three the unit cell volume increased at a rate greater than the formula weight of the asymmetric unit such that crystal density decreased from 1.823 to 1.619 Mg/m3.
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References
Olah GA, Narang SC, Olah JA, Lammertsma K (1982) Proc Natl Acad Sci USA 79:4487–4494
Olah GA, Malhotra R, Narang SC (1989) Nitration, methods and mechanisms. VCH, New York
Agrawal JP, Hodgson RD (2007) Organic chemistry of explosives. Wiley, West Sussex
Urbański T (1984) Chemistry and technology of explosives, vol IV. Pergamon Press, New York
Köhler J, Meyer R (1993) Explosives, 4th edn. VCH, Weinheim, p 380
Ott DG, Benziger TM (1987) J Energy Mater 5:343–354
Cady HH, Larson AC (1965) Acta Cryst 18:485–496
Maiti A, Pagoria PF, Gash AE, Han TY, Orme CA, Gee RH, Fried LE (2008) Phys Chem Chem Phys 10:5050–5056
Hoffman DM, Willey TM, Mitchell AR, Depiero SC (2008) J Energy Mater 26:139–162
Benziger TM (1981) Int Jahrestagung ICT, Karlsruhe, Germany July 1–3, 1981, pp 491–493
Benziger TM (1977) US Patent 4,032,377
Bellamy AJ, Ward SJ, Golding P (2002) Propellants Explos Pyrotech 27:49–58
Straessler NA (2010) Synth Commun 40:2513–2519
Anulewicz-Ostrowska R, Krygowski TM, Cyrański MK, Matuszewska MP (1999) Polish J Chem 73:1895–1901
Sun CC (2007) J Pharm Sci 96:1043–1052
Wolff JJ, Gredel F, Irngartinger H, Dreier T (1996) Acta Cryst (Sect C) 52C:3225–3227
Parrish DA, Deschamps JR, Gilardi RD, Butcher RJ (2008) Cryst Growth Des 8:57–62
Vrcelj RM, Sherwood JN, Kennedy AR, Gallagher HG, Gelbrich T (2003) Cryst Growth Des 3:1027–1032
Acknowledgments
This research was supported by the Department of Defense: Strategic Environmental Research and Development Program (SERDP Project # WP 1582) performed under ATK Aerospace Systems Contract W912HQ-07-C-0018, and by the Naval Research Laboratory.
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Deschamps, J.R., Straessler, N.A. Structure of O-Methyl-trinitrophloroglucinol Derivatives. J Chem Crystallogr 41, 971–975 (2011). https://doi.org/10.1007/s10870-011-0027-5
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DOI: https://doi.org/10.1007/s10870-011-0027-5